28447-16-7

Basic information

• Product Name: 4-(pyridin-3-yl)-but-3-en-2-one
• Synonyms: 4-(pyridin-3-yl)-but-3-en-2-one
• CAS NO: 28447-16-7
• Molecular Formula: C9H9NO
• Molecular Weight: 147.17386
• Mol File: 28447-16-7.mol
• Article Data: 16

Chemical Properties

• Boiling Point: 280.5 °C at 760 mmHg
• Flash Point: 130.9 °C
• Appearance: /
• Density: 1.072 g/cm³
• CAS DataBase Reference: 4-(pyridin-3-yl)-but-3-en-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: 4-(pyridin-3-yl)-but-3-en-2-one(28447-16-7)
• EPA Substance Registry System: 4-(pyridin-3-yl)-but-3-en-2-one(28447-16-7)

Safety Data

• Hazardous Substances Data: 28447-16-7(Hazardous Substances Data)

Usage

General Description

4-(Pyridin-3-yl)-but-3-en-2-one, also known as 3-Pyridin-4-yl-3-buten-2-one, is an organic compound with the molecular formula C9H7NO. It is a yellow solid that is sparingly soluble in water but soluble in organic solvents. 4-(Pyridin-3-yl)-but-3-en-2-one is commonly used in the synthesis of pharmaceuticals, agrochemicals, and other fine chemicals due to its versatile reactivity and functional groups. It can undergo various chemical reactions, including nucleophilic addition and substitution, making it a valuable intermediate in organic synthesis. Additionally, it also exhibits potential biological activity, making it a target for drug discovery and development. 4-(Pyridin-3-yl)-but-3-en-2-one has applications in medicinal chemistry and drug design, and its structural versatility makes it an important building block in the synthesis of complex organic molecules.

Upstream product

• 500-22-1 3-pyridinecarboxaldehyde 
• 67-64-1 acetone 
• 1439-36-7 1-triphenylphosphoranylidene-2-propanone 
• 2091-46-5 triphenyl(prop-2-ynyl)phosphonium bromide 
• 626-55-1 3-Bromopyridine 
• 78-94-4 methyl vinyl ketone 
• 123-75-1 pyrrolidine 
• 54756-29-5 2-acetyl-3ξ-[3]pyridyl-acrylic acid ethyl ester 
• 105900-69-4 2-(hydroxy-[3]pyridyl-methyl)-acetoacetic acid ethyl ester 
• 78-95-5 chloroacetone 

Downstream Products

• 300805-77-0 C₉H₁₁NO 

Relevant articles and documents

An Efficient Procedure for the Synthesis of trans-2-, -3-, and -4-Pyridalacetones

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Balanced dual acting compounds targeting aromatase and estrogen receptor α as an emerging therapeutic opportunity to counteract estrogen responsive breast cancer

Breast Cancer (BC) is a leading cause of death in women, currently affecting 13% of female population worldwide. First-line clinical treatments against Estrogen Receptor positive (ER+) BC rely on suppressing estrogen production, by inhibiting the aromatase (AR) enzyme, or on blocking estrogen-dependent pro-oncogenic signaling, by targeting Estrogen Receptor (ER) α with selective Modulators/Degraders (SERMs/SERDs). The development of dual acting molecules targeting AR and ERα represents a tantalizing alternative strategy to fight ER + BC, reducing the incidence of adverse effects and resistance onset that limit the effectiveness of these gold-standard therapies. Here, in silico design, synthesis, biological evaluation and an atomic-level characterization of the binding and inhibition mechanism of twelve structurally related drug-candidates enable the discovery of multiple compounds active on both AR and ERα in the sub-μM range. The best drug-candidate 3a displayed a balanced low-nanomolar IC50 towards the two targets, SERM activity and moderate selectivity towards a BC cell line. Moreover, most of the studied compounds reduced ERα levels, suggesting a potential SERD activity. This study dissects the key structural traits needed to obtain optimal dual acting drug-candidates, showing that multitarget compounds may be a viable therapeutic option to counteract ER + BC.

Sequential Two-Step Stereoselective Amination of Allylic Alcohols through the Combination of Laccases and Amine Transaminases

A sequential two-step chemoenzymatic methodology for the stereoselective synthesis of (3E)-4-(het)arylbut-3-en-2-amines in a highly selective manner and under mild reaction conditions is described. The approach consists of oxidation of the corresponding racemic alcohol precursors by the use of a catalytic system made up of the laccase from Trametes versicolor and the oxy-radical TEMPO, followed by the asymmetric reductive bio-transamination of the corresponding ketone intermediates. Optimisation of the oxidation reaction, exhaustive amine transaminase screening for the bio-transaminations and the compatibility of the two enzymatic reactions were studied in depth in search of a design of a compatible sequential cascade. This synthetic strategy was successful and the combinations of enzymes displayed a broad substrate scope, with 16 chiral amines being obtained in moderate to good isolated yields (29–75 %) and with excellent enantiomeric excess values (94 to >99 %). Interestingly, both amine enantiomers can be achieved, depending on the selectivity of the amine transaminase employed in the system.